callophycoic acid E (CHEBI:65561)

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CHEBI:65561 - callophycoic acid E

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ChEBI ID	CHEBI:65561
ChEBI Name	callophycoic acid E
Stars
Definition	A dibenzooxepine diterpenoid that is hexahydrodibenzo[b,e]oxepine-2-carboxylic acid with an isolated double bond between positions 6 and 6a and is substituted by a bromo, a 2-[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]ethyl and a methyl group at positions 9, 10 and 10 respectively (the 9S,10S,10aR stereoisomer). It is isolated from the Fijian red alga Callophycus serratus and exhibits antibacterial, antimalarial and anticancer activities.
Last Modified	3 December 2012
Downloads	Molfile

Formula	C27H34Br2O3
Net Charge	0
Average Mass	566.374
Monoisotopic Mass	564.08747
SMILES	[H][C@@]12Cc3cc(C(=O)O)ccc3OC=C1CC[C@H](Br)[C@@]2(C)CC[C@@H]1C(=C)CC[C@H](Br)C1(C)C
InChI	InChI=1S/C27H34Br2O3/c1-16-5-9-23(28)26(2,3)20(16)11-12-27(4)21-14-19-13-17(25(30)31)6-8-22(19)32-15-18(21)7-10-24(27)29/h6,8,13,15,20-21,23-24H,1,5,7,9-12,14H2,2-4H3,(H,30,31)/t20-,21-,23+,24+,27+/m1/s1
InChIKey	PSYSMHVCBGMCIW-FBHGCBBZSA-N

Species of Metabolite	Component	Source	Comments
Callophycus serratus (ncbitaxon:632897)	-	PubMed (17715978)

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:	antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	callophycoic acid E (CHEBI:65561) has role antibacterial agent (CHEBI:33282)
	callophycoic acid E (CHEBI:65561) has role antimalarial (CHEBI:38068)
	callophycoic acid E (CHEBI:65561) has role antineoplastic agent (CHEBI:35610)
	callophycoic acid E (CHEBI:65561) has role metabolite (CHEBI:25212)
	callophycoic acid E (CHEBI:65561) is a benzoic acids (CHEBI:22723)
	callophycoic acid E (CHEBI:65561) is a cyclic ether (CHEBI:37407)
	callophycoic acid E (CHEBI:65561) is a dibenzooxepine (CHEBI:38926)
	callophycoic acid E (CHEBI:65561) is a diterpenoid (CHEBI:23849)
	callophycoic acid E (CHEBI:65561) is a organobromine compound (CHEBI:37141)

IUPAC Name
(9S,10S,10aR)-9-bromo-10-{2-[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-10-methyl-7,8,9,10,10a,11-hexahydrodibenzo[b,e]oxepine-2-carboxylic acid

Manual Xrefs	Databases
27023091	ChemSpider

Registry Numbers	Sources
Reaxys:11167775	Reaxys

Citations